The Maillard Reaction in Food Chemistry: Current Technology and Applications

104 Pages·2018·4.83 MB·English

by  Dongliang Ruan

SPRINGER BRIEFS IN MOLECULAR SCIENCE
CHEMISTRY OF FOODS
Dongliang Ruan
Hui Wang
Faliang Cheng
The Maillard
Reaction in Food
Chemistry
Current Technology
and Applications
SpringerBriefs in Molecular Science
Chemistry of Foods
Series editor
Salvatore Parisi, Industrial Consultant, Palermo, Italy
The series Springer Briefs in Molecular Science: Chemistry of Foods presents
compacttopicalvolumesintheareaoffoodchemistry.Theserieshasaclearfocus
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biology offoods are not part of its scope. The Briefs volumes in the series aim at
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overviewonthechemistryrelatedtospecifictopicsinthisarea.Typicaltopicsthus
include:
– Compound classes in foods—their chemistry and properties with respect to the
foods (e.g. sugars, proteins, fats, minerals, …)
– Contaminants and additives in foods—their chemistry and chemical
transformations
– Chemical analysis and monitoring offoods
– Chemical transformations in foods, evolution and alterations of chemicals in
foods, interactions between food and its packaging materials, chemical aspects
of the food production processes
– Chemistry and the food industry—from safety protocols to modern food
production
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concerned with food chemistry. Many volume topics address professionals and
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Dongliang Ruan Hui Wang
(cid:129)
Faliang Cheng
The Maillard Reaction
in Food Chemistry
Current Technology and Applications
123
Dongliang Ruan Faliang Cheng
DongguanUniversity of Technology DongguanUniversity of Technology
Dongguan,Guangdong, China Dongguan,Guangdong, China
HuiWang
Lacombe Research Centre
Agriculture andAgri-FoodCanada
Lacombe,AB, Canada
ISSN 2191-5407 ISSN 2191-5415 (electronic)
SpringerBriefs inMolecular Science
ISSN 2199-689X ISSN 2199-7209 (electronic)
Chemistry of Foods
ISBN978-3-030-04776-4 ISBN978-3-030-04777-1 (eBook)
https://doi.org/10.1007/978-3-030-04777-1
LibraryofCongressControlNumber:2018962133
©TheAuthor(s),underexclusivelicensetoSpringerNatureSwitzerlandAG2018
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Preface
Maillardreaction,thewell-knownnon-enzymaticreactionbetweenreducingsugars
andproteins,isoneofthemostimportantreactionsinfoodsciences.Aminoacids,
peptidesandproteinsarethekeyconstituentsoffoodandalsodirectlycontributeto
the changes in colour, flavor, and nutritive value but also for the formation of
stabilizing and mutagenic compounds during thermal or enzymatic reactions in
production,processingandstorageoffood.Proteinsalsocontributesignificantlyto
thephysicalpropertiesoffoodthroughtheirabilitytobuildorstabilizegels,foams
and emulsions properties. Due to the complexity of the Maillard reaction, mass
spectrometry(MS)isausefulandpowerfultechnologytocharacterizetheMaillard
reaction products and we have apply MS-based technologies to systematically
investigate Maillard reaction from amino acids, peptides, proteins, to characterize
the Maillard reaction products and to identify the modification sites of proteins.
Studies demonstrate that glucosylation increased emulsification activity index and
emulsifyingstabilityindex.ThepresentinvestigationdemonstratesthatMS-related
technologies are important tools to analyze and characterize the Maillard reaction
products and functional properties offood proteins.
Dongguan, China Dongliang Ruan
Lacombe, Canada Hui Wang
Dongguan, China Faliang Cheng
v
Acknowledgements
The authors would like to thank Prof. C. Y. Ma and Dr. Ivan K. Chu for their
invaluable advices, constant encouragement and inspiring discussion during the
studies and writing process. The authors would like to thank Prof. Michael Siu,
Dr. Wang Mingfu, Dr. K. H. Sze and Dr. Huang Junchao for their stimulating
discussion and helpful comments in the research.
The authors would like to thank my friends, colleagues and members of our
laboratories for reading and comments on chapters: Dr. Siu Shiu On, Dr. Emily
Choi, Dr. Song Tao, Dr. Edward Lau and Dr. Corey N. W. Lam for the valuable
friendship, help and support.
The authors would like to express my appreciation to all the staff and technical
servicecrewintheSchoolofBiologicalScienceandtheChemistryDepartment,the
University of Hong Kong.
Finally, the authors would like to dedicate the whole-heart thanks to Hui, Irene
and Max, and all the family members for their love, care and understanding
throughout my research.
vii
Contents
1 The Maillard Reaction . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1
1.1 Introduction . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1
1.2 The Maillard Reaction and Food Properties . . . . . . . . . . . . . . . . 2
1.3 The Chemistry of the Maillard Reaction. . . . . . . . . . . . . . . . . . . 2
1.4 Conditions Affecting the Maillard Reaction . . . . . . . . . . . . . . . . 5
1.5 The Analysis of MRPs . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 7
1.5.1 ESI-MS and MALDI-TOF-MS. . . . . . . . . . . . . . . . . . . . 8
1.5.2 MS Characterization of ARPs. . . . . . . . . . . . . . . . . . . . . 9
1.5.3 Protein Glycation and Glycation Site Analysis. . . . . . . . . 10
1.6 Summary . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 12
References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 13
2 Characterization of the Maillard Reaction in Amino
Acid–Sugar Systems . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 23
2.1 Introduction . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 23
2.2 MS Analysis of Amino Acid–Sugar System. . . . . . . . . . . . . . . . 23
a
2.3 Structure Determination of Glucosylated N -Acetyl-Lysine
by Nuclear Magnetic Resonance (NMR) Spectroscopy . . . . . . . . 25
2.4 ARPs in Amino Acid–Sugar Systems . . . . . . . . . . . . . . . . . . . . 28
2.4.1 MS/MS of ARPs with D-Glucose . . . . . . . . . . . . . . . . . . 28
2.4.2 MS/MS of ARPs with Disaccharides. . . . . . . . . . . . . . . . 28
2.5 MS/MS and MS3 of ARPs . . . . . . . . . . . . . . . . . . . . . . . . . . . . 30
2.6 Summary . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 30
References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 32
3 Characterization of Glycated Lysine in Peptide–Sugar System. . . . . 33
3.1 Introduction . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 33
3.2 Solid-Phase Peptide Synthesis (SPPS) . . . . . . . . . . . . . . . . . . . . 34
3.2.1 Synthesis Procedure. . . . . . . . . . . . . . . . . . . . . . . . . . . . 34
3.2.2 Cleavage of the Peptide . . . . . . . . . . . . . . . . . . . . . . . . . 35
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x Contents
3.3 ESI-MS Analysis . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 35
3.4 Effects of the Maillard Reaction . . . . . . . . . . . . . . . . . . . . . . . . 35
3.5 Fragmentation Sugar Moieties . . . . . . . . . . . . . . . . . . . . . . . . . . 36
3.6 Fragmentation of Peptide Moieties. . . . . . . . . . . . . . . . . . . . . . . 43
3.6.1 Fragmentation of [M-84+H]+ . . . . . . . . . . . . . . . . . . . . . 43
3.6.2 MS3 of Glucosylated Di-peptides . . . . . . . . . . . . . . . . . . 45
3.6.3 MS3 Spectra of [M-84+H]+ from Glucosylated
Tri-Peptides. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 46
3.7 Fragmentation of Lysine-Containing Tetra-Peptides . . . . . . . . . . 49
3.8 Summary . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 53
References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 53
4 Determination of the Maillard Reaction Sites and Properties’
Effects of Lysozyme . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 55
4.1 Introduction . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 55
4.2 Sample Preparation. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 56
4.3 MS . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 57
4.3.1 MALDI-TOF-MS . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 57
4.3.2 MALDI-TOF/TOF-MS. . . . . . . . . . . . . . . . . . . . . . . . . . 57
4.3.3 Nano-LC-QqTOF-MS . . . . . . . . . . . . . . . . . . . . . . . . . . 57
4.4 Emulsifying Properties . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 58
4.5 Differential Scanning Calorimetry (DSC) . . . . . . . . . . . . . . . . . . 59
4.6 Deconvolution of ESI-MS Spectra. . . . . . . . . . . . . . . . . . . . . . . 60
4.7 MS Analysis of Intact Lysozyme. . . . . . . . . . . . . . . . . . . . . . . . 60
4.8 Effects of Glucosylation on Lysozyme. . . . . . . . . . . . . . . . . . . . 65
4.8.1 Effect on Emulsifying Properties. . . . . . . . . . . . . . . . . . . 65
4.8.2 Effect on Thermal Properties . . . . . . . . . . . . . . . . . . . . . 67
4.9 Characterization of Glycation of Lysozyme . . . . . . . . . . . . . . . . 68
4.9.1 MALDI-TOF-MS . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 68
4.9.2 MALDI-TOF/TOF-MS. . . . . . . . . . . . . . . . . . . . . . . . . . 72
4.9.3 Nano-LC-MS/MS . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 73
4.10 Summary . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 79
References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 80
Abbreviations
12-crown-4 1,4,7,10-tetraacyclododecane
ACN Acetonitrile
CID Collision induced dissociation
ECD Electron capture dissociation
EI Electron impact
ESI Electrospray
ESI* Emulsifying stability index
ETD Electron transfer dissociation
eV Electron voltage
FAB Fast atom bombardment
FTICR Fourier transform ion cyclotron resonance
GC Gas chromatography
HPLC High pressure/performance liquid chromatography
HRP Horseradish peroxidase
LIT Linear ion trap
m/z Mass to charge ratio
MALDI Matrix-assisted laser desorption/ionization
MeOH Methanol
MS Mass spectrometry
MS2 or MS/MS Tandem mass spectrometry
MSn Multistage tandem mass spectrometry
NMR Nuclear magnetic resonance
NP Normal phase
PMF Peptide mass fingerprint
PNGaseF Peptide N-glycosidase F
PTMs Posttranslational modifications
Q Quadrupole
QIT Quadrupole ion trap
QqQ Triple quadrupole
RNaseB Ribonuclease B
xi